Naphthoquinone-based hydrazone hybrids: synthesis and potent activity against cancer cell lines

2020 ◽  
Vol 16 ◽  
Author(s):  
Délis Galvão Guimarães ◽  
Arlan de Assis Gonsalves ◽  
Larissa Araújo Rolim ◽  
Edigênia Cavalcante Araújo ◽  
Victória Laysna dos Anjos Santos ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Biological Activities ◽  
Supporting Electrolyte ◽  
Cancer Cell Lines ◽  
Molecular Structures ◽  
Cytotoxic Activities ◽  
Electrochemical Studies ◽  
Ic50 Values

Background: Natural naphthoquinones have shown diversified biological activities including antibacterial, antifungal, antimalarial, and cytotoxic activities. However, they are also compounds with acute cytotoxicity, immunotoxicity, carcinogenesis, and cardio- and hepatotoxicity, then the modification at their redox center is an interesting strategy to overcome such harmful activity. Objective: In this study, four novel semisynthetic hydrazones, derived from the isomers α- and β-lapachones (α and β, respectively) and coupled with the drugs hydralazine (HDZ) and isoniazid (ACIL), were prepared, evaluated by electrochemical methods and assayed for anticancer activity. Method: The semisynthetic hydrazones were obtained and had their molecular structures established by NMR, IR, and MS. Anticancer activity was evaluated by cell viability determined by reduction of 3-(4,5-dimethyl-2-thiazol)-2,5-diphenyl-2H-tetrazolium bromide (MTT). The electrochemical studies, mainly cyclic voltammetry, were performed, in aprotic and protic media. Result: The study showed that the compounds 2, 3, and 4 were active against at least one of the cancer cell lines evaluated, being compounds 3 and 4 the most cytotoxic. Toward HL-60 cells, compound 3 was 20x more active than β-lapachone, and 3x more cytotoxic than doxorubicin. Furthermore, 3 showed an SI value of 39.62 for HL-60 cells. Compound 4 was active against all cancer cells tested, with IC50 values in the range 2.90–12.40 μM. Electrochemical studies revealed a profile typical of self-protonation and reductive cleavage, dependent on the supporting electrolyte. Conclusion: These results therefore indicate that compounds 3 and 4 are strong candidates as prototypes of new antineoplastic drugs.

scholarly journals Synthesis, Cytotoxic Activity, Crystal Structure, DFT Studies and Molecular Docking of 3-Amino-1-(2,5-dichlorophenyl)-8-methoxy-1H-benzo[f]chromene-2-carbonitrile

Crystals ◽  
2021 ◽  
Vol 11 (2) ◽  
pp. 184
Author(s):  
Menna El Gaafary ◽  
Tatiana Syrovets ◽  
Hany M. Mohamed ◽  
Ahmed A. Elhenawy ◽  
Ahmed M. El-Agrody ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Dna Methyltransferase ◽  
Human Cancer ◽  
Theoretical Calculations ◽  
Cancer Cell Lines ◽  
Molecular Structures ◽  
Cytotoxic Activities ◽  
X Ray

The target compound 3-amino-1-(2,5-d ichlorophenyl)-8-methoxy-1H-benzo[f]-chromene-2-carbonitrile (4) was synthesized via a reaction of 6-methoxynaphthalen-2-ol (1), 2,5-dichlorobenzaldehyde (2), and malononitrile (3) in ethanolic piperidine solution under microwave irradiation. The newly synthesized β-enaminonitrile was characterized by FT-IR, 1H NMR, 13C NMR, mass spectroscopy, elemental analysis and X-ray diffraction data. Its cytotoxic activity was evaluated against three different human cancer cell lines MDA-MB-231, A549, and MIA PaCa-2 in comparison to the positive controls etoposide and camptothecin employing the XTT cell viability assay. The analysis of the Hirshfeld surface was utilized to visualize the reliability of the crystal package. The obtained results confirmed that the tested molecule revealed promising cytotoxic activities against the three cancer cell lines. Furthermore, theoretical calculations (DFT) were carried out with the Becke3-Lee-Yang-parr (B3LYP) level using 6-311++G(d,p) basis. The optimization geometry for molecular structures was in agreement with the X-ray structure data. The HOMO-LUMO energy gap of the studied system was discussed. The intermolecular-interactions were studied through analysis of the topological-electron-density(r) using the QTAIM and NCI methods. The novel compound exhibited favorable ADMET properties and its molecular modeling analysis showed strong interaction with DNA methyltransferase 1.

scholarly journals Structure-Dependent Cytotoxic Effects of Eremophilanolide Sesquiterpenes

2017 ◽  
Vol 12 (5) ◽  
pp. 1934578X1701200 ◽  
Author(s):  
M. Teresa Agulló-Ortuño ◽  
Carmen E. Díaz ◽  
Azucena González-Coloma ◽  
Matías Reina
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Antitumor Agents ◽  
Cancer Cell Lines ◽  
Cytotoxic Activities ◽  
Cytotoxic Action ◽  
Cytotoxic Effects ◽  
Ic50 Values ◽  
Comparative Structure ◽  
Dose Dependent

The aim of this research was to determine the cytotoxic action of sixteen structurally-related eremophilane-type sesquiterpenes, isolated from several species of Senecio, against a panel of cancer cell lines. The cytotoxic activities were evaluated by WST-1 test and the IC50 values calculated. The investigated compounds exerted dose-dependent cytotoxic actions against selected cancer cell lines and no-tumoral HS5 cell line. The comparative structure-activity relationships demonstrated the importance of C-1, C-6, and C-8 substituents in the molecule. Our results show that eremophilane-type sesquiterpenes may represent an important source of novel potential antitumor agents due to their pronounced cytotoxic actions towards malignant cells.

scholarly journals Cytotoxic Sterols from Philippine Mushrooms

2020 ◽  
Vol 32 (5) ◽  
pp. 1197-1202
Author(s):  
Consolacion Y. Ragasa ◽  
Glenn G. Oyong ◽  
Maria Carmen S. Tan ◽  
Mariquit M. De Los Reyes ◽  
Maria Ellenita G. De Castro
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Human Cancer ◽  
Dermal Fibroblast ◽  
Cancer Cell Lines ◽  
Cytotoxic Activities ◽  
Cell Viability Assay ◽  
Ic50 Values ◽  
Ht 29 ◽  
Mcf 7

Ergosterol peroxide (1) and ergosterol (2) were commonly isolated as the major compounds of Philippine mushrooms. Sterols 1 and 2 from the dichloromethane extract of Geastrum triplex and Termitomyces clypeatus, respectively, were evaluated for their cytotoxic activities against four human cancer cell lines, viz., breast cancer (MCF-7), colon cancer (HT-29), leukemia (THP-1), and small lung cell carcinoma (H69PR), and a human normal cell line, human dermal fibroblast-neonatal (HDFn), using the PrestoBlue® cell viability assay. Compounds 1 and 2 exhibited the strongest activities against HT-29 with IC50 values of 1.79 and 2.98 μg/mL, respectively, while Zeocin gave an IC50 of 4.89 μg/mL. These compounds also exhibited strong antiproliferative effects against MCF-7 with IC50 values of 4.13 for 1 and 4.20 μg/mL for compound 2, comparable to Zeocin with IC50 = 3.68 μg/mL. Only moderate cytotoxicity resulted when compounds 1 and 2 were tested against H69PR with IC50 values of 7.78 and 6.83 μg/mL, respectively, while Zeocin exhibited an IC50 of 9.81 μg/mL. Furthermore, compounds 1 and 2 showed no effects against THP-1 (IC50 > 100 μg/mL), while Zeocin showed an IC50 of 4.73 μg/mL. Although compounds 1 and 2 have been reported to exhibit different bioactivities in previous studies, the cancer cell lines tested and/or the polarities of the solvents for extraction varied. Therefore, comparisons of the cytotoxic activities of compounds 1 and 2 with earlier studies could not be made extensively.

scholarly journals In VitroAntibacterial, Antioxidant, and Cytotoxic Activities ofParthenium hysterophorusand Characterization of Extracts by LC-MS Analysis

2014 ◽  
Vol 2014 ◽  
pp. 1-10 ◽  
Author(s):  
Shashank Kumar ◽  
Sanjay Pandey ◽  
Abhay K. Pandey
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Biological Activities ◽  
Beta Carotene ◽  
Cancer Cell Lines ◽  
Salmonella Typhi ◽  
Cytotoxic Activities ◽  
Plant Parts ◽  
Colon Cancer Cell Lines

Present work reports the biological activities ofP. hysterophorusleaf, stem, flower, and root. Dried samples were sequentially extracted with many solvents. Hexane (HX), benzene (BZ), and chloroform (CH) extracts of leaf showed considerable antibacterial activity againstStreptococcus mutans(MTCC 497),Proteus vulgaris(MTCC 7299), andSalmonella typhi(MTCC 3917). Flower extracts exhibited presence of higher amount of flavonoids (13.9–59.6 μgQE/mg) followed by leaf, stem, and root. Stem (HX, BZ, and CH), leaf ethanol (ET), and root (HX, BZ, and CH) fractions showed noticeable antioxidant capacity in phosphomolybdate assay. Most of the extracts demonstrated beta carotene bleaching inhibition capability. BZ, ethyl acetate (EA), and ET fractions of leaves, stem aqueous (AQ), and flower EA extracts showed membrane protective activities (40–55%). Middle fractions of the plant parts displayed moderate antihemolytic potential. Most of the flower extracts exhibited cytotoxic activity (80–100%) against lung and colon cancer cell lines. Root (HX and ET) and leaf ET extracts showed considerable inhibition (90–99%) of colon and ovary cancer cell lines. The LC-MS scan demonstrated presence of different compounds showing 3–20 min retention time. The study revealed considerable antibacterial, antioxidant, lipo-protective, antihemolytic, and anticancer potential in all parts ofP. hysterophorus.

scholarly journals Biological Effects of Glucosinolate Degradation Products from Horseradish: A Horse that Wins the Race

Biomolecules ◽  
2020 ◽  
Vol 10 (2) ◽  
pp. 343 ◽  
Author(s):  
Marijana Popović ◽  
Ana Maravić ◽  
Vedrana Čikeš Čulić ◽  
Azra Đulović ◽  
Franko Burčul ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Degradation Products ◽  
Human Cancer ◽  
Biological Activities ◽  
Biological Effects ◽  
Cancer Cell Lines ◽  
Cytotoxic Activities ◽  
Minimal Inhibitory Concentrations

Horseradish degradation products, mainly isothiocyanates (ITC) and nitriles, along with their precursors glucosinolates, were characterized by GC-MS and UHPLC-MS/MS, respectively. Volatiles from horseradish leaves and roots were isolated using microwave assisted-distillation (MAD), microwave hydrodiffusion and gravity (MHG) and hydrodistillation (HD). Allyl ITC was predominant in the leaves regardless of the isolation method while MAD, MHG, and HD of the roots resulted in different yields of allyl ITC, 2-phenylethyl ITC, and their nitriles. The antimicrobial potential of roots volatiles and their main compounds was assessed against sixteen emerging food spoilage and opportunistic pathogens. The MHG isolate was the most active, inhibiting bacteria at minimal inhibitory concentrations (MICs) from only 3.75 to 30 µg/mL, and fungi at MIC50 between <0.12 and 0.47 µg/mL. Cytotoxic activity of volatile isolates and their main compounds were tested against two human cancer cell lines using MTT assay after 72 h. The roots volatiles showed best cytotoxic activity (HD; IC50 = 2.62 μg/mL) against human lung A549 and human bladder T24 cancer cell lines (HD; IC50 = 0.57 μg/mL). Generally, 2-phenylethyl ITC, which was tested for its antimicrobial and cytotoxic activities along with two other major components allyl ITC and 3-phenylpropanenitrile, showed the best biological activities.

scholarly journals Ethiopian Medicinal Plants Traditionally Used for the Treatment of Cancer; Part 3: Selective Cytotoxic Activity of 22 Plants against Human Cancer Cell Lines

Molecules ◽  
2021 ◽  
Vol 26 (12) ◽  
pp. 3658
Author(s):  
Solomon Tesfaye ◽  
Hannah Braun ◽  
Kaleab Asres ◽  
Ephrem Engidawork ◽  
Anteneh Belete ◽  
...  
Keyword(s):  
Medicinal Plants ◽  
Cell Lines ◽  
Cancer Cell ◽  
Mononuclear Cells ◽  
Cancer Cell Lines ◽  
Cytotoxic Activities ◽  
Cell Lung Carcinoma ◽  
Carcinoma Of The Esophagus ◽  
Ic50 Values ◽  
Mcf 7

Medicinal plants have been traditionally used to treat cancer in Ethiopia. However, very few studies have reported the in vitro anticancer activities of medicinal plants that are collected from different agro-ecological zones of Ethiopia. Hence, the main aim of this study was to screen the cytotoxic activities of 80% methanol extracts of 22 plants against human peripheral blood mononuclear cells (PBMCs), as well as human breast (MCF-7), lung (A427), bladder (RT-4), and cervical (SiSo) cancer cell lines. Active extracts were further screened against human large cell lung carcinoma (LCLC-103H), pancreatic cancer (DAN-G), ovarian cancer (A2780), and squamous cell carcinoma of the esophagus (KYSE-70) by using the crystal violet cell proliferation assay, while the vitality of the acute myeloid leukemia (HL-60) and histiocytic lymphoma (U-937) cell lines was monitored in the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) microtiter assay. Euphorbia schimperiana, Acokanthera schimperi, Kniphofia foliosa, and Kalanchoe petitiana exhibited potent antiproliferative activity against A427, RT-4, MCF-7, and SiSo cell lines, with IC50 values ranging from 1.85 ± 0.44 to 17.8 ± 2.31µg/mL. Furthermore, these four extracts also showed potent antiproliferative activities against LCLC-103H, DAN-G, A2780, KYSE-70, HL-60, and U-937 cell lines, with IC50 values ranging from 0.086 to 27.06 ± 10.8 µg/mL. Hence, further studies focusing on bio-assay-guided isolation and structural elucidation of active cytotoxic compounds from these plants are warranted.

scholarly journals Streptomyces griseus KJ623766: A Natural Producer of Two Anthracycline Cytotoxic Metabolites β- and γ-Rhodomycinone

Molecules ◽  
2021 ◽  
Vol 26 (13) ◽  
pp. 4009
Author(s):  
Ahmed S. Abu Zaid ◽  
Ahmed E. Aleissawy ◽  
Ibrahim S. Yahia ◽  
Mahmoud A. Yassien ◽  
Nadia A. Hassouna ◽  
...  
Keyword(s):  
Ethyl Acetate ◽  
Cell Lines ◽  
Cancer Cell ◽  
Ethyl Acetate Extract ◽  
Biological Activities ◽  
Streptomyces Griseus ◽  
Cancer Cell Lines ◽  
Cytotoxic Activities ◽  
Chemical Structures ◽  
Bioassay Guided Fractionation

Background: This study aimed to produce, purify, structurally elucidate, and explore the biological activities of metabolites produced by Streptomyces (S.) griseus isolate KJ623766, a recovered soil bacterium previously screened in our lab that showed promising cytotoxic activities against various cancer cell lines. Methods: Production of cytotoxic metabolites from S. griseus isolate KJ623766 was carried out in a 14L laboratory fermenter under specified optimum conditions. Using a 3-(4,5-dimethylthazol-2-yl)-2,5-diphenyl tetrazolium-bromide assay, the cytotoxic activity of the ethyl acetate extract against Caco2 and Hela cancer cell lines was determined. Bioassay-guided fractionation of the ethyl acetate extract using different chromatographic techniques was used for cytotoxic metabolite purification. Chemical structures of the purified metabolites were identified using mass, 1D, and 2D NMR spectroscopic analysis. Results: Bioassay-guided fractionation of the ethyl acetate extract led to the purification of two cytotoxic metabolites, R1 and R2, of reproducible amounts of 5 and 1.5 mg/L, respectively. The structures of R1 and R2 metabolites were identified as β- and γ-rhodomycinone with CD50 of 6.3, 9.45, 64.8 and 9.11, 9.35, 67.3 µg/mL against Caco2, Hela and Vero cell lines, respectively. Values were comparable to those of the positive control doxorubicin. Conclusions: This is the first report about the production of β- and γ-rhodomycinone, two important scaffolds for synthesis of anticancer drugs, from S. griseus.

The Antileukemic Potential of New Derivatives of 5-Fluoro-1H-Indole-2,3-Dione-3-Thiosemicarbazone on in Vitro Cell Lines

Blood ◽  
2008 ◽  
Vol 112 (11) ◽  
pp. 5055-5055
Author(s):  
Serap Erdem Kuruca ◽  
Nilgun Karali ◽  
Beyza Cetin ◽  
Sabriye Karadenizli ◽  
Zeynep Karakas
Keyword(s):  
Chronic Myeloid Leukemia ◽  
Cell Lines ◽  
Cancer Cell ◽  
Myeloid Leukemia ◽  
Biological Activities ◽  
Cancer Cell Lines ◽  
Lymphoma Cell ◽  
B Lymphoma ◽  
Ic50 Values ◽  
Allyl Derivative

Abstract 1H-Indole-2,3-dione (isatin) is an endogenous compound identified in many organisms, possesses a wide range of biological activities. Biological properties of isatin include a range of actions in brain and offer protection against certain types of infections. This molecule has a versatile moiety that displays diverse biological activities, including anticancer activity. The discovery of numerous biologically active 3-substituted 2-indolinones led in the past decade to extensive synthesis of related compounds and as a result, anticancer agents were developed. In particular, among the 5-substituted analogs tested in the growth inhibitions against several human cancer cell lines, 5-halide, methoxy and trifluoromethoxy groups containing 3-substituted 2-indolinones show high antiproliferative effects. For this purpose, we first synthesized twelve 5-fluoro-1H-indole-2,3-dione-3-thiosemicarbazones that antituberculosis activities were shown previously by our teamwork and we researched anticancer drug potential in this study. The cytotoxic effects of twelve thiosemicarbazone derivatives were investigated by MTT assay in chronic myeloid leukemia cell lines (K562, HL60), B-lymphoma cell lines (P3HR1) and in vincristine resistant forms. The IC50 values (IC50 is a concentration that kills 50% of cells) were calculated from dose-response curve according to cytotoxicity index. The effectiveness of thiosemicarbazone derivatives were evaluated by comparing IC50 values in leukemic cell lines. All of the compounds were found cytotoxic in B-lymphoma cell lines (P3HR1, P3HR1Vin) in range 0.95–2.41 μM. However, the allyl derivative of thiosemicarbazones has cytotoxic activity in all the cancer cell lines (K562, K562Vin, HL-60, P3HR1, P3HR1Vin) that were tested. As a result, 5-fluoro-1H-indole-2,3-dione-3-thiosemicarbazones derivates might have chemotherapeutic drug potential in B-lymphoma patients. The allyl derivative of thiosemicarbazones has benefit both B-lymphoma and chronic myeloid leukemia patients in a large spectrum.

scholarly journals Monarubins A–C from the Marine Shellfish-Associated Fungus Monascus ruber BB5

Marine Drugs ◽  
2020 ◽  
Vol 18 (2) ◽  
pp. 100
Author(s):  
Yan-Qin Ran ◽  
Wen-Jian Lan ◽  
Yi Qiu ◽  
Qi Guo ◽  
Gong-Kan Feng ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Carcinoma Cell ◽  
2D Nmr ◽  
Cancer Cell Lines ◽  
Cytotoxic Activities ◽  
Monascus Ruber ◽  
Carcinoma Cell Lines ◽  
Ic50 Values ◽  
New Compounds

Three new compounds, monarubins A–C (1, 6 and 13), together with ten known compounds, including four alkaloids (2–5), two isocoumarins (7 and 8) and four polyketides (9–12), were isolated from marine shellfish-associated fungus Monascus ruber BB5. The structures were determined on the basis of the 1D and 2D NMR, MS, UV and IR data. The absolute configurations of compounds 3, 6 and 13 were determined by ECD calculations. The NMR data of compounds deoxyhydroxyaspergillic acid (3) and 2-hydroxy-6-(1-hydroxy-1-methylpropyl)-3-sec-buthylpyrazine (4) were first reported. All of the isolated compounds were evaluated for their cytotoxic activities against human nasopharyngeal carcinoma cell lines CNE1, CNE2, SUNE1 and HONE1 and hepatocellular carcinoma cell lines QGY7701 and HepG2. Monarubin B (6) displayed potent cytotoxicities against the cancer cell lines HepG2 and QGY7701 with IC50 values of 1.72 and 0.71 μΜ, respectively; lunatinin (7) showed moderate cytotoxic activities against the cancer cell lines HepG2, QGY7701 and SUNE1 with the IC50 values of 9.60, 7.12 and 28.12 μΜ, respectively.

scholarly journals Microbial Transformation of Galangin Derivatives and Cytotoxicity Evaluation of Their Metabolites

Catalysts ◽  
2021 ◽  
Vol 11 (9) ◽  
pp. 1020
Author(s):  
Fubo Han ◽  
Yina Xiao ◽  
Ik-Soo Lee
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Microbial Transformation ◽  
Cancer Cell Lines ◽  
Resonance Spectroscopy ◽  
Cytotoxic Activities ◽  
Alpinia Officinarum ◽  
Spectroscopic Analyses ◽  
Ic50 Values ◽  
Mcf 7

Galangin (1), 3-O-methylgalangin (2), and galangin flavanone (3), the major bioactive flavonoids isolated from Alpinia officinarum, were biotransformed into one novel and four known metabolites (4–8) by application of the fungal strains Mucor hiemalis and Absidia coerulea as biocatalysts. Their structures were characterized by extensive spectroscopic analyses including one- and two-dimensional nuclear magnetic resonance spectroscopy and mass spectrometry. Compounds 1–7 were evaluated for their cytotoxic activities against cancer cell lines using the MTT assay. The new compound 3-O-methylgalangin-7-O-β-D-glucopyranoside (6) exhibited the most potent cytotoxic activity against MCF-7, A375P, B16F10, B16F1, and A549 cancer cell lines with the IC50 values at 3.55–6.23 μM.

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